Ethanol → 2-Ethyl-3-hydroxy-1-[2-(alpha-methylpropionyloxy)ethyl]pyridin-4-one

HRID 374451Notes

Reaction equation

HRID 374451 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[C:10]=1[CH2:24][CH3:25])C1C=CC=CC=1.CCO.CCOC(C)=O>CN(C)C=O.[Pd]>[CH2:24]([C:10]1[N:11]([CH2:16][CH2:17][O:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH:12]=[CH:13][C:14](=[O:15])[C:9]=1[OH:8])[CH3:25]

Participants

6

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 189971733-Benzyloxy-2-ethyl-1-[2-(alpha-methylpropionyloxy)ethyl]pyridin-4-one

Product 1

HCID 97949942-Ethyl-3-hydroxy-1-[2-(alpha-methylpropionyloxy)ethyl]pyridin-4-oneYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

3-Benzyloxy-2-ethyl -1-[2-(α-methylpropionyloxy)ethyl]pyridin-4-one was dissolved in 35 ml of dimethylformamide and about 0.1 g of palladium on activated charcoal (5%) was added. The solution was left under H2 for four days and the reaction was monitored by tlc (silica; 50% EtOH:50% EtOAc). The solution was filtered three times and rotary evaporated under high vacuum. The oily residue was then treated with activated charcoal in ethyl acetate, filtered and rotary evaporated to dryness. After crystallization from ethyl acetate the pure title compound was obtained in 37% yield, m.p., i.r., n.m.r. and mass spectra as quoted in Example 4.

Workup

  1. filtrationThe solution was filtered three times
  2. customrotary evaporated under high vacuum
  3. additionThe oily residue was then treated with activated charcoal in ethyl acetate
  4. filtrationfiltered
  5. customrotary evaporated to dryness
  6. customAfter crystallization from ethyl acetate the pure title compound
  7. customwas obtained in 37% yield, m.p., i.r

Sources & evidence

ORD record
ord-3c25c27b53e04b1dbf9261f67d1bc0a2
Source dataset
uspto-grants-1996_01
Patent number
US05480894

Reaction notes

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